Regioselective debenzylation of C-glycosyl compounds by boron trichloride |
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| Authors: | Xie Juan Ménand Mickaël Valéry Jean-Marc |
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| Institution: | Synthèse, Structure et Fonction des Molécules Bioactives, CNRS UMR 7613, Equipe Chimie des Glucides, Université Pierre et Marie Curie, 4 Place Jussieu, F-75005 Paris, France. joanne.xie@ppsm.ens-cachan.fr |
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| Abstract: | Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl(3) follows the order: C-4>or=C-2>C-6>C-3 for C-glucopyranosyl derivatives and C-3>or=C-4>C-6>C-2 for C-galactopyranosyl derivatives. Preparatively useful selective debenzylation at secondary positions was possible after careful control of reaction conditions. |
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| Keywords: | Boron trichloride C-Glycosyl compounds Regioselective debenzylation |
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